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Reactions of Grignard reagents with aldehydes and ketones

T1 - Synthesis of cyclic enones via direct palladium-catalyzed aerobic dehydrogenation of ketones

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Reductive Amination of Aldehydes and Ketones with …

AB - Highly enantioselective reduction of aliphatic chloro ketones catalyzed by Thermoanaerobium brockii alcohol dehydrogenase (TBADH) afforded the corresponding S chloro alcohols, which are new and useful chiral bifunctional building blocks. The synthetic potential of these compounds was illustrated by syntheses of several optically pure cyclic ethers. In particular, (S)-(+)-5-chloropentan-2-ol was used for the total synthesis of (+)-(S,S)-(cis-6-methyltetrahydropyran-2-yl) acetic acid, a natural constituent of the perfume material civet. Two of the key steps in the synthesis involve organopalladium chemistry: a Pd(0)-catalyzed intramolecular allylic etherification followed by a Pd(II)-catalyzed Wacker oxidation of the disubstituted olefin.

Synthesis of Dispirotrioxolanes by the Ozonolysis of O-Methyloximes and Cyclic Ketones

α-Chloro(diazo)acetate can be readily used in an intermolecular ring expansion catalyzed by a boron Lewis acid to construct α-chlorinated medium-size cyclic ketones. This intermolecular Tiffeneau–Demjanov reaction proceeds in good yield from easily prepared or commercially available starting materials and allows the concomitant formation of a tetrasubstituted stereocenter.

Synthesis of cyclic ketones via iron tricarbonyl …

Synthesis of Dispirotrioxolanes by the Ozonolysis of O-Methyloximes and Cyclic Ketones

AB - α,β-Unsaturated carbonyl compounds are versatile intermediates in the synthesis of pharmaceuticals and biologically active compounds. Here, we report the discovery and application of Pd(DMSO) 2(TFA) 2 as a catalyst for direct dehydrogenation of cyclohexanones and other cyclic ketones to the corresponding enones, using O 2 as the oxidant. The substrate scope includes heterocyclic ketones and several natural-product precursors.

N2 - α,β-Unsaturated carbonyl compounds are versatile intermediates in the synthesis of pharmaceuticals and biologically active compounds. Here, we report the discovery and application of Pd(DMSO) 2(TFA) 2 as a catalyst for direct dehydrogenation of cyclohexanones and other cyclic ketones to the corresponding enones, using O 2 as the oxidant. The substrate scope includes heterocyclic ketones and several natural-product precursors.

SYNTHESIS 0F CYCLIC KETONES VIA IRON TRICARBONYL COMPLEXES B.F.G

This is areliable generalization for comparisions of aldehydes and ketones.

α-Chloro(diazo)acetate can be readily used in an intermolecular ring expansion catalyzed by a boron Lewis acid to construct α-chlorinated medium-size cyclic ketones. This intermolecular Tiffeneau–Demjanov reaction proceeds in good yield from easily prepared or commercially available starting materials and allows the concomitant formation of a tetrasubstituted stereocenter.

AB - The efficient preparation of a range of cyclic (aryl ether ketone)s containing the 1,2-dibenzoylbenzene moiety via the nucleophilic aromatic substitution route with the use of the pseudo-high dilution principle was developed. Chemical transformation of the 1,2-dibenzoylbenzene moiety of these cyclic (aryl ether ketone)s led to the preparation of novel cyclic (aryl ether phthalazine)s and cyclic (aryl ether isoquinoline)s. The preparation of cyclic (aryl ether ketone)s from 4,4′-difluorobenzophenone and 1,3-bis(4-fluorobenzoyl)benzene is also discussed. Detailed structural characterization of these novel oligomers by matrix-assisted laser desorption ionization time-of-flight mass spectrometry (MALDI-TOF-MS), 13C and 1H NMR, GPC, and HPLC confirmed the cyclic nature and revealed the composition of the oligomeric mixtures prepared. MALDI-TOF-MS, which enables the detection of oligomers with mass up to 5000 Da, was shown to be a very powerful tool for the analysis and proof of the cyclic nature of the oligomers. Thermoanalyses show that most of these oligomers exhibit a high degree of crystallinity while their corresponding polymers are amorphous.

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  • Synthesis of Aldehydes & Ketones - Chemistry LibreTexts

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    Gleiter* "Synthesis of [6.8]3Cyclacene: Conjugated Belt and Model for an unusual Type of Carbon Nanotube"

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Acid-catalyzed condensations of cyclic ketones: …

N2 - The efficient preparation of a range of cyclic (aryl ether ketone)s containing the 1,2-dibenzoylbenzene moiety via the nucleophilic aromatic substitution route with the use of the pseudo-high dilution principle was developed. Chemical transformation of the 1,2-dibenzoylbenzene moiety of these cyclic (aryl ether ketone)s led to the preparation of novel cyclic (aryl ether phthalazine)s and cyclic (aryl ether isoquinoline)s. The preparation of cyclic (aryl ether ketone)s from 4,4′-difluorobenzophenone and 1,3-bis(4-fluorobenzoyl)benzene is also discussed. Detailed structural characterization of these novel oligomers by matrix-assisted laser desorption ionization time-of-flight mass spectrometry (MALDI-TOF-MS), 13C and 1H NMR, GPC, and HPLC confirmed the cyclic nature and revealed the composition of the oligomeric mixtures prepared. MALDI-TOF-MS, which enables the detection of oligomers with mass up to 5000 Da, was shown to be a very powerful tool for the analysis and proof of the cyclic nature of the oligomers. Thermoanalyses show that most of these oligomers exhibit a high degree of crystallinity while their corresponding polymers are amorphous.

Synthesis of Diverse β-Quaternary Ketones via …

N2 - Highly enantioselective reduction of aliphatic chloro ketones catalyzed by Thermoanaerobium brockii alcohol dehydrogenase (TBADH) afforded the corresponding S chloro alcohols, which are new and useful chiral bifunctional building blocks. The synthetic potential of these compounds was illustrated by syntheses of several optically pure cyclic ethers. In particular, (S)-(+)-5-chloropentan-2-ol was used for the total synthesis of (+)-(S,S)-(cis-6-methyltetrahydropyran-2-yl) acetic acid, a natural constituent of the perfume material civet. Two of the key steps in the synthesis involve organopalladium chemistry: a Pd(0)-catalyzed intramolecular allylic etherification followed by a Pd(II)-catalyzed Wacker oxidation of the disubstituted olefin.

Stereocontrolled synthesis of carbocyclic compounds …

The previously unknown product of photochemical [2+2]-cycloaddition of 2,5-bis[(E)-(3-pyridyl)methylidene]cyclopentanone was synthesized and characterized by spectroscopic methods and X-ray diffraction.

Stereocontrolled synthesis of carbocyclic compounds with a ..

T1 - Synthesis and characterization of novel cyclic (aryl ether ketone)s, cyclic (aryl ether phthalazine)s, and cyclic (aryl ether isoquinoline)s

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